Indole → HCID 18780221, compound

HRID 345669Notes

Reaction equation

HRID 345669 reaction equation
C[Mg]I.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.Br[C:14]1[C:15](=[O:29])[NH:16][C:17](=[O:28])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>C(OCC)C.C1C=CC=CC=1>[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]2[C:15](=[O:29])[NH:16][C:17](=[O:28])[C:18]=2[C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[CH:5]1

Participants

6

Reactant 3

HCID 798IndoleHCID 18780241HCID 18780241, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 18780221HCID 18780221, compoundYield 0.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

1.4 ml of a 3M solution of methylmagnesium iodide in diethyl ether was added to a solution of 360 mg indole in 20 ml of benzene under nitrogen. After stirring at room temperature for 10 minutes 300 mg of 3-bromo-4-(4-nitrophenyl)-1H-pyrrole-2,5-dione were added and the resulting mixture was heated to reflux for 4 days. After cooling the solution was evaporated and the residue was partitioned between dichloromethane and 2M hydrochloric acid. The organic phase was washed with water, dried and evaporated. The residue was purified on silica gel with dichloromethane and 1% methanol in dichloromethane and then with 20% methanol/water on Hypersil to give 3 mg of 3-(3-indolyl)-4-(4-nitrophenyl)-1H-pyrrole-2,5-dione, m.p. 125° C. (decomposition).

Workup

  1. additionwere added
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 days
  4. temperatureAfter cooling the solution
  5. customwas evaporated
  6. customthe residue was partitioned between dichloromethane and 2M hydrochloric acid
  7. washThe organic phase was washed with water
  8. customdried
  9. customevaporated
  10. customThe residue was purified on silica gel with dichloromethane and 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-71a127b425274df1a7f45a54e215080b
Source dataset
uspto-grants-1991_10
Patent number
US05057614

Reaction notes

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